Question 1

Which of the following is the major product when 1-phenylethanol is treated with PCC (pyridinium chlorochromate) in dichloromethane?

Accepted Answer

Acetophenone ($$C_6H_5COCH_3)$$

Question 2

When cyclohexene reacts with mCPBA (meta-chloroperoxybenzoic acid), what is the major product?

Accepted Answer

Cyclohexene oxide (an epoxide)

Question 3

Which reagent would best convert a primary alcohol to an aldehyde without further oxidation to a carboxylic acid?

Accepted Answer

PCC (pyridinium chlorochromate)

Question 4

What is the major organic product when 1-methoxypropane is heated with HI?

Accepted Answer

1-propanol and methyl iodide

Question 5

Which of the following best describes the mechanism for the acid-catalyzed opening of an epoxide with water?

Accepted Answer

SN1 attack at the more substituted carbon after protonation

Question 6

A solution of 2-butanol is treated with NaOCl (bleach) and acetic acid. What is the major product?

Accepted Answer

2-butanone ($$CH_3CH_2COCH_3)$$

Question 7

Which of the following ethers will react fastest with HI to give alkyl iodides?

Accepted Answer

tert-Butyl methyl ether

Question 8

What is the expected product when benzyl alcohol is treated with Na_2Cr_2O_7 and H_2SO_4?

Accepted Answer

Benzoic acid

Question 9

Which of the following statements about the Williamson ether synthesis is correct?

Accepted Answer

It is an SN2 reaction between an alkoxide and a primary alkyl halide.

Question 10

Which of the following is a correct statement about the oxidation of thiols?

Accepted Answer

Thiols are oxidized to disulfides ($$R-S-S-R) $$under mild oxidizing conditions.

Question 11

A patient is exposed to ethylene oxide in a laboratory accident. Which functional group is most likely to be formed in their body as a result of nucleophilic attack by water?

Accepted Answer

Alcohol

Question 12

Which of the following reagents would best convert a secondary alcohol to a ketone?

Accepted Answer

NaOCl/acetic acid

Question 13

What is the major product when 1,2-epoxypropane is treated with aqueous acid?

Accepted Answer

1,2-propanediol

Question 14

Which of the following is the best method to prepare tert-butyl methyl ether?

Accepted Answer

Reacting sodium tert-butoxide with methyl iodide

Question 15

Which of the following is a correct statement about the acid-catalyzed dehydration of alcohols?

Accepted Answer

It forms an alkene via an E1 mechanism.

Question 16

What is the major product when 2-methyl-2-butanol is heated with concentrated H_2SO_4?

Accepted Answer

2-methyl-2-butene

Question 17

Which of the following is the correct product when phenol reacts with NaOH and then with methyl iodide?

Accepted Answer

Anisole ($$C_6H_5OCH_3)$$

Question 18

Which of the following is the major product when 1-butanol is treated with NaOCl and acetic acid?

Accepted Answer

Butanal ($$CH_3CH_2CH_2CHO)$$

Question 19

Which of the following statements about ethers is correct?

Accepted Answer

Ethers are generally unreactive except towards strong acids like HI and HBr.

Reactions of Alcohols, Ethers, Epoxides, Amines, and Thiols: Mechanisms and Major Products

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